This episode starts out with Ralph parading through the streets with an imaginary bear. To him, it is "Parade Day," and he is parading through the streets saying "Happy Parade Day!," until his imaginary bear friend points out a hedge. He goes through it and sees a golf course. He goes to school the next day and tells Bart, Nelson and Millhouse that it's the best playground ever. He says that there are Easter eggs and baby cars that anyone can drive and clowns wearing clown pants. They decide to go check it out and they don't know how to get through the hedge and Bart says "I've seen my dad do this," and goes through the hedge, referring to the scene of Homer disapearing through a hedge in the episode, Homer Loves Flanders. When they go through they see a golf course, and sees Jimbo sucking up to Doctor Hibbert, and gets 20 bucks for doing so. He asks how he got the money and he says he's a caddy, so he goes to the clubhouse and gets a job.
His first job is cadding to Kent Brockman who tips him 20 dollars. The next scene shows them at the table eating and praising Bart. He shows off his wad of money and his rubber band is straining. Homer shows off his "Wad" and the rubber band snaps, revealing that it is stuffed with non static dryer sheets. After that it shows Marge and Maggie watching Bart do his job, and Marge couldn't help but overhear Bart sucking up to the golfers. She hasn't seen her son suck up before and asks if he does this to all of the golfers. He says it just for the money, but Marge still doesn't like him sucking up. He next caddies to Judge Snyder, who tips him 50 bucks, the biggest tip he has gotten yet.
The next scene shows the family at an ice cream shop, where Bart puts money in the jar and says, "Buy yourself a bigger tip jar." Marge pulls Homer out, asking him if it bothers him that Bart is sucking up to which Homer replies, "sucking up is the American way". Then Marge tells him to make Bart give up his job. Homer goes to Bart and asks him to quit and Bart gives him 20 bucks and says they never had this conversation. The next scene shows Bart in a pool with Nelson and Milhouse and they ask him what hes gonna buy next. He tells him that he will buy "the patented ultra freedom", a 4×4. The group asks If they can have rides, and he says that they need their own wads.
He gets a caddy job for the club owner Bildorf whom never tips less that 100 bucks. He gives him the idea for making this religious meeting place for no taxes. Meanwhile, Lisa is helping Marge with making an online petition. Bildorf and Bart turn the club into a religious meeting place. Bart tries to caddy for the him but he says that since Marge is no longer a threat, he's going to go back to Chadlington, his previous caddy, so Bart tears up the green with his new 4x4.